Department of Chemistry , Stanford University , Stanford , California 94305-5080 , United States.
J Am Chem Soc. 2019 Mar 27;141(12):4811-4814. doi: 10.1021/jacs.9b00788. Epub 2019 Mar 15.
The C19-oxo-functionalized eburnane alkaloids display unique chemical structure and interesting biological activity. Herein, we report a divergent enantioselective strategy to access these alkaloids by use of a challenging palladium-catalyzed asymmetric allylic alkylation of an N-alkyl-α,β-unsaturated lactam. 19-( S)-OH-Δ-vincamone (phutdonginin), (-)-19-OH-eburnamine, (+)-19-oxoeburnamine, and (+)-19-OH-eburnamonine (1-4) have been concisely synthesized for the first time in 11 to 13 steps.
C19-氧化功能化的鹅掌楸烷生物碱具有独特的化学结构和有趣的生物活性。在此，我们报告了一种发散的对映选择性策略，通过使用具有挑战性的钯催化的 N-烷基-α,β-不饱和内酰胺的不对称烯丙基烷基化反应来获得这些生物碱。19-（S）-OH-Δ-vinchamonine（phutdonginin），（-）-19-OH-eburnamine，（+）-19-oxoeburnamine 和（+）-19-OH-eburnamonine（1-4）首次以 11 至 13 步的步骤简洁合成。
